The C-glycosylation reactions of different protected stilbene monomers with anomeric acetylated glucosyl donor were promoted by BF₃•OEt₂, and their corresponding aryl C-glucosides were stereoselectively synthesized. The kind and stablity of phenolic protecting groups in stilbenes directly influenced the product yields of 10-C-β-glucosides and 12-C-β-glucosides. Final global deprotection of stilbene C-glucoside intermediates was unsuccessful, but the structures of 10-C-β-glucoside product were confirmed by the selective debenzylation of brominated resveratrol 10-C-β-glucoside analogue.

Key words: resveratrol C-glucoside, stilbene, aryl C-glycosylation, protecting groups, synthesis